Transition-Metal-Catalyzed Addition of Organosulfur Compounds to Alkynes and Alkenes: Catalysis and Catalyst Poisons

The addition of heteroatom compounds to alkynes and alkenes is an atom-efficient method of carbon-heteroatom bond formation and is widely used as a fundamental synthetic method for the construction of functional molecules. Nevertheless, examples of transition-metal-catalyzed addition reactions of group 16 heteroatom compounds to carbon-carbon unsaturated bonds have been limited due to the widespread belief that organic sulfur and selenium compounds are representative catalyst poisons. In recent decades, however, several seminal catalytic reactions of sulfur compounds have been developed, providing important insights into catalysis and poisons. Therefore, this paper focuses on the transition-metal-catalyzed addition of organosulfur compounds to alkynes and alkenes, gains comprehensive insights into the catalysis and catalyst poisons, and proposes concepts for the development of transition-metal-catalyzed reactions of group 16 heteroatom compounds. Transition-metal-catalyzed addition of organosulfur compounds to carbon-carbon unsaturated bonds has been considered as one of the challenging reactions due to the catalyst poisons. Recently, novel systems have been investigated to suppress the catalyst poisons. This article highlights the pioneering studies on the catalytic addition of organosulfur compounds to alkynes and alkenes and describes their catalysis and catalyst poisons.image